KR20090018828A - Glyceryl and Glycolic Acid Compounds - Google Patents

Abstract

A composition comprising a glyceryl salicylate compound and/or a glycol salicylate compound. The compositions can be used to reduce the amount of moisture evaporated from skin, protect the skin from UV light, and treat aged or damaged skin.

Description

Glyceryl and Glycolic Acid Compounds {GLYCERYL AND GLYCOL ACID COMPOUNDS}

This application claims the benefit of priority of US Provisional Serial No. 60 / 747,760, filed May 19, 2006, the contents of which are incorporated by reference.

The present invention generally relates to compounds that can be used in compositions such as cosmetic skin care compositions. Compounds may be included in acid molecules bound to glycerol or glycol molecules via ester bonds.

Due to aging, chronic exposure to harmful environmental factors, or malnutrition, the visual appearance, physical properties, and physiological function of the skin can change in ways that are considered visually undesirable. The most known and obvious changes include the progression of fine lines and wrinkles, loss of elasticity, increased sag, loss of firmness, loss of color uniformity or hue, rough surface feel, and mottled pigment formation. Less obvious but foreseeable changes that occur due to skin age or tolerate chronic environmental damage are reductions in general cell and tissue vitality, decreases in cell replication rates, reduced skin blood flow rates, reduced moisture content, structure and function Cumulative errors, changes in normal regulation of the general biochemical pathways, and a decrease in the ability of the skin to repair and repair itself. Many changes in the appearance and function of the skin are due to changes in the outer epithelial layer of the skin, while others are due to changes under the dermis.

Several different approaches have been used to treat damaged skin due to aging, environmental factors, chemicals, or malnutrition. These approaches can often have drawbacks such as severe irritation to the skin or skin toxicity.

Summary of the Invention

The present invention overcomes the deficiencies in the art. In a non-limiting aspect, the present invention generally relates to compounds that can be used in compositions such as cosmetic and pharmaceutical compositions. In some embodiments, compounds may be included in acid molecules bound to glycerol or glycol molecules via ester linkages. General and specific structures of these compounds are known throughout this specification and have been added to this section by reference.

In some embodiments, the compound may be added into the composition. The composition may be a cosmetic composition or a pharmaceutical composition. The composition can typically be applied to the skin. The composition can be included in a cosmetic vehicle. Non-limiting examples of cosmetic vehicles are known in other sections of this specification and are known to those of ordinary skill in the art. Examples of cosmetic vehicles include emulsions (eg, hydrophilic emulsifying (oil-in-water) and lipophilic emulsifying (water-in-oil) emulsions), creams, lotions, solutions (eg, water-soluble or hydroalcoholic solutions). ), Anhydrous bases (eg, lipsticks or powders), gels, and ointments. In other non-limiting embodiments, the compositions of the present invention can be included in anti-aging, cleaning, or moisturizing products. The composition may also be formulated for topical skin application at least 1, 2, 3, 4, 5, 6, 7, or more times per day during use. In another aspect of the invention, the composition may be stored stably or in a stable color, or both.

In some embodiments, the compositions of the present invention may comprise from about 0.001% to about 20% of the glyceryl / acid or glycol / acid compound, or a combination thereof, by weight or volume. However, it should be appreciated that the amount of compound in the composition may vary below, within, or above this range based on the desired result (e.g., 1, 2, 3, 4, by weight or volume of the composition). , 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 , 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 55, 60, 65, 70 , 75, 80, 85, 90, 95, 96, 97, 98, 99%, or greater). Thus, the amount of glyceryl / acid or glycol / acid compound may comprise, by weight or volume, less than 0.001% or more than 5%. In another aspect, the composition comprises 0.002, 0.003, 0.004 ... 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, by weight or volume of glyceryl or glycol salicylate or combinations thereof. , 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 95, 96, 97, 98, 99 %, Or above, or any range that can be derived therefrom. In another embodiment, the compositions of the present invention may further comprise carnitine molecules. Carnitine molecules may be acylated (eg, acetyl-1-carnitine). In some aspects, the ratio of any component in the composition as compared to the other component is about 1: 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 11: 1, 12: 1, 13: 1, 14: 1, 15: 1, 16: 1, 17: 1, 18: 1, 19: 1, 20: 1, 21: 1, 22: 1, 23: 1, 24: 1, 25: 1, 26: 1, 27: 1, 28: 1, 29: 1, 30: 1, 31: 1, 32: 1, 33: 1, 34: 1, 35: 1, 36: 1, 37: 1, 38: 1, 39: 1, 40: 1, 50: 1, 60: 1, 70: 1, 80: 1, 90: 1, 100: 1, or more, or any number that can be derived therefrom. In another aspect, the ratio of any component in the composition as compared to the other component is about 1: 2, 1: 3, 1: 4, 1: 5, 1: 6, 1: 7, 1: 8, 1: 9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1: 20, 1:21, 1:22, 1:23, 1:24, 1:25, 1:26, 1:27, 1:28, 1:29, 1:30, 1:31, 1:32, 1:33, 1:34, 1:35, 1:36, 1:37, 1:38, 1:39, 1:40, 1:50, 1:60, 1:70, 1:80, 1: 90, 1: 100, or more, or any number that can be derived there.

The composition of the present invention may also be modified to have a desired oxygen radical absorption capacity (ORAC) value. In some non-limiting aspects, the compositions of the present invention comprise at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 , 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35, 40, 45, 50, 55, 60, 70, 80, 90, 95, 100, 200, 300, 400 Which can be derived from, or there, 500, 600, 700, 800, 900, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 15000, 20000, 30000, 50000, 100000 or more It can be altered to have ORAC values per mg in any range.

In another non-limiting aspect of the invention, the composition may further comprise vitamins, minerals, essential fatty acids, amino acids (including essential and non-essential amino acids), flavonoids, and / or proteins, or combinations thereof. Non-limiting examples of vitamins include B vitamins (eg Bl, B2, B6, B12, niacin, folic acid, biotin, and pantothenic acid), vitamin C, vitamin D, vitamin E (eg, tocopherol or toco) Peryl acetate), vitamin A (eg, palmitate, retinyl palmitate, or retinoic acid), and vitamin K. Non-limiting examples of minerals include iron, potassium, phosphorus, magnesium, manganese, selenium, and calcium. Non-limiting examples of essential fatty acids include omega 3 (linolenic acid), omega 6 (linoleic acid) and omega 9 (oleic acid) essential fatty acids, or combinations thereof. Non-limiting examples of amino acids include essential amino acids (eg, lysine, leucine, isoleucine, methionine, phenylalanine, threonine, tryptophan, valine, histidine, or arginine) and non-essential amino acids (eg, serine, asparagine, glutamine, aspart) Acid, glutamic acid, alanine, tyrosine, cysteine, glycine, or proline). Non-limiting examples of flavonoids include anthocyanin compounds (eg, cyanidin-3-glucoside and cyanidin-3-rutinoside).

In a non-limiting aspect, the composition can have a pH of about 6 to about 9. In another aspect, the pH can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14. The composition may comprise triglycerides. Non-limiting examples include small, medium, and large chain triglycerides. In some aspects, the triglycerides are medium chain triglycerides (eg caprylic capric triglycerides). The composition may also include a preservative. Non-limiting examples of preservatives include methylparabens, propylparabens, or mixtures of methylparabens and propylparabens.

Also known are methods of treating or preventing a skin condition comprising topical application of a composition comprising a glyceryl / acid compound and / or a glycol / acid compound, wherein the topical application of the composition is to treat the skin condition. Non-limiting examples of skin conditions include itching, spider veins, melanoma, blotch, senile purpura, keratosis, blemishes, blotches, fine lines or wrinkles, nodules, sun damaged skin, dermatitis (seborrheic dermatitis, Molecular dermatitis, contact dermatitis, atopic dermatitis, deprived dermatitis, perioral dermatitis, and congestive dermatitis), psoriasis, folliculitis, rosacea, acne, pus, erysipelas, Erythrasma, eczema, and other inflammatory skin conditions. In some non-limiting aspects, the skin condition can be caused by exposure to UV light, age, radiation, chronic sun exposure, air pollutants, wind, cold, heat, compounding, pathology, smoking, or nutritional deficiencies. The skin can be facial skin or skin other than the face (eg, arms, legs, hands, chest, back, feet, etc.). The method may further comprise identifying a person in need of skin treatment. A person can be a man or a woman. The age of a person is at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75 , 80, 85, 90, 95, or over age, or any range that can be derived therefrom.

The composition of the present invention can also be used in a method for exfoliating the skin. This allows the user to exfoliate dead skin cells and also promote the natural sloughing process of the skin. The advantage of this process is that it reveals and exposes "young," newer skin. The shedding process helps to clear the pores, keep the skin clean, and reduce the rapid spread of acne.

The method of the present invention may also typically include applying an effective amount to: increasing the rate of stratum corneum conversion of the skin; Reduced skin roughness; Increased collagen synthesis in fibroblasts; Increasing cellular antioxidant defense mechanisms (eg, exogenous addition of antioxidants reinforces the reduction of cellular antioxidants such as catalase and glutathione in skin cells (eg keratinocytes, melanocytes, Langerhans cells, etc.). Can be supplemented, or prevented, which will reduce or prevent oxidative damage to skin, cells, proteins, and lipids); Interfere with melanin production in melanocytes; Reducing or preventing oxidative damage to the skin (including reducing the amount of lipid peroxides and / or protein oxidation in the skin); Increase in adhering plaque decay, leading to an increase in keratinocyte detachment; Cytokine, hyaluronic acid, cell proliferation, collagen production and epidermal proliferation; Normalizing keratinocyte aggregation; Increase in lipid synthesis within the intercellular range; Target sebum in sebaceous glands; And fibroblast activation.

The compositions of the present invention may also be used alone in a prescription plan or in combination with other compositions (eg, skin care compositions). For example, the compositions of the present invention may be applied in the morning and / or in the evening at predetermined intervals and / or amounts. Alternatively, the composition of the present invention may be applied in the morning and the second skin care composition may be applied in the evening and vice versa.

Also disclosed are methods of using glyceryl / acid compounds and glycol / acid compounds as moisturizers, film-forming agents, UV absorbers, and / or skin therapeutics. For example, the compound may maintain and / or increase the moisture (eg, moisture content) of the skin. The compound can also smooth the skin. The compound may form a membrane or barrier on the outer membrane of the skin that may reduce or prevent evaporation of water from the skin. In some aspects, the membrane can have tactile properties that make the skin feel soft or smooth. The compound can also be used as a UV absorber and in a method of increasing the UV absorbing properties of a composition, such as a sunscreen composition. The compound can be used in a method of increasing the SPF of a sunscreen composition. In some aspects, the compounds may be used to increase the efficiency of the sunscreen products present and / or sunscreens used in such products. Alternatively, the compound may be used as the sunscreen agent alone. In some embodiments, the compounds may be used in a method to reduce or prevent chemical or physical deterioration of cosmetic compositions caused by ultraviolet light. The compounds and / or compositions of the present invention can disperse or absorb a broad spectrum of UV radiation. For example, the compounds and / or compositions may absorb or disperse UVA (about 315-400 nm), UVB (about 280-315) and / or UVC (about 10-280 nm) light. In some aspects, the compounds and / or compositions range from about 1 to about 400 nm, or any integer or range therein (eg, 2, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 399) can absorb or disperse UV light.

Also kits may be envisioned comprising the compositions of the present invention. In some embodiments, the composition is included in a container. The container may be a bottle, dispenser, or package. The container may dispense a predetermined amount of the composition. In some aspects, the composition is dispersed in a spray or mist, a soft lump, or a liquid. The container may include an indication on its surface. Markings may be words, abbreviations, pictures, or symbols.

In addition, a product comprising the composition of the present invention can be envisioned. In a non-limiting aspect, the product can be a cosmetic product. Cosmetic products can be those described in other sections of this specification or those known to those skilled in the art. Non-limiting examples of products include moisturizers, creams, lotions, emollients, foundations, night creams, lipsticks, cleaners, toners, sunscreens, masks, or anti-aging products.

Any embodiments discussed herein may be met with respect to any method or composition of the present invention, and vice versa. In addition, the composition of the present invention can be used to achieve the method of the present invention.

The term "alkyl" includes straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl heteroatom-substituted cycloalkyl groups, and cycloalkyl heteroatom-substituted alkyl groups.

The term "alkoxy" includes groups having the structure -OR, where R is an alkyl group. Non-limiting examples of alkoxy groups include -OCH ₃ , -OCH ₂ CH ₃ , -OCH ₂ CH ₂ CH ₃ , -OCH (CH ₃ ) ₂ , -OCH (CH ₂ ) ₂ , and the like.

The term "hydroxyalkyl" includes alkyl groups having one or more hydroxy groups.

The term “about” or “approximately” is defined closest to the understanding by one skilled in the art, and in one non-limiting embodiment the term is defined to be within 10%, within 5%, within 1%, and / or within 0.5%.

The term "inhibition" or "reduction" or any change in these terms, when used in the claims and / or specification, includes any measurable reduction or complete inhibition to achieve a desired result.

The term "efficient" means that when the term is used in the specification and / or claims, it is suitable to achieve a desired, predicted or intended result.

The use of the word "a" or "an" may refer to the meaning of "one" when used in connection with the term "comprising" in the claims and / or specification, but it also refers to "one or more," "at least one," and It is also consistent with the meaning of "one or more than one."

Although the specification only supports alternatives and definitions indicating “and / or”, the use of the term “or” in the claims is intended to refer to “and / or” except where it is evident that only the alternatives are expressly indicated or alternatives are mutually excluded. I'm used to it.

As used herein and in claim (s), the word "comprising" (and any form of "comprising", such as "comprise" and "comprises"), "having" (And any form of "having", eg "have" and "has"), any form of "including" (and "including", eg "includes" and "include" ) Or "containing" (and any form of "comprising", such as "contains" and "contain") does not include or limit, and does not exclude additional, non-cited elements or method steps. .

Other objects, features and advantages of the present invention will become apparent from the following detailed description. However, it is to be understood that the description and examples are given by way of illustration only, while showing specific embodiments of the invention. In addition, it is contemplated that changes and modifications within the spirit and scope of the invention will be apparent to those skilled in the art from this specification.

Detailed description of the invention

In today's image-conscious society, people are constantly looking for products that can protect or improve the visual appearance of their skin. Often, aged skin, uneven skin tone, or skin damaged by environmental factors such as UV light, chronic sun exposure, environmental contaminants, compounds, pathology, or smoking is associated with unattractive skin. . The compounds of the present invention can be used in all types of cosmetic compositions / formulations for treating, maintaining, or preventing the appearance of aged or damaged skin.

For example, the compounds of the present invention may have a wide variety of uses in compositions applied to the skin. Non-limiting examples include compounds used as moisturizers, film-forming agents, UV absorbers, and skin treatments. As a moisturizer, the compound can help to maintain and / or increase the moisture of the skin, thereby making the skin softer and supple. The compounds may also be used as lubricants to the skin to treat, reduce, or prevent skin exfoliation and dry skin.

As a film-forming agent, the compounds can be used to form a film or barrier on the outer surface of the skin. This may be an advantage of reducing or preventing evaporation of water from the skin. In addition, the membrane may have tactile properties that make the skin feel soft or smooth.

As UV absorbers, compounds can be used to protect cosmetic compositions from chemical and physical deterioration caused by ultraviolet light. The compounds may also be used as sunscreens in sunscreen compositions. The compounds may also increase the sun protection factor (SPF) of sunscreen compositions that already include sunscreens.

As skin treatments, the compounds can be used as active ingredients in topical skin care compositions. Non-limiting examples of skin conditions that can be treated with the compounds of the present invention are known throughout the specification.

These and other aspects of the invention are further described in detail without limitation.

A. Glyceryl / Acid and Glycol / Acid Compounds

1. Glyceryl / Acid Compound

Glyceryl / acid compounds of the invention may be derived from glycerol molecules having the structure:

Glycerol

The acid portion of the glyceryl / acid compound may be linked via ester bonds of the OH group of the glycerol molecule and the COOH group of the acid molecule. In a non-limiting aspect, the glyceryl / acid compound can have the following general chemical structure:

Wherein R, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are each independently H, acid molecule, hydroxy, halogen, oxo (eg ether), alkoxy, silyloxy, acyl , Aryl, acetyl, carbonyl, cyano, heterocyclyl, amido, aminocarbonyl, amino, -NH-alkyl, -N (alkyl) ₂ , -NH- (substituted alkyl), -N- (substituted Alkyl) ₂ , -NH-aryl, -N (aryl) ₂ , azido, trialkylsilyloxy, acyloxy, acylamino, bis-acylamino, ester, NO, NO ₂ , or sulfo (eg, Thioether, thioester, thiocarbonyl, sulfonamido, sulfonyl, etc.). In some aspects, the acid molecule is selected from the group consisting of salicylic acid, cinnamic acid, and benzoic acid, and derivatives and substituted acids thereof. Other non-limiting examples of acids that can be used in the context of the present invention are described in International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed., 2004, which is added by reference. In some aspects, at least one of R, R ₄ , and R ₆ is an acid, R and R ₄ are an acid, R and R ₆ are an acid, R ₄ and R ₆ are an acid, or R, R ₄ , and R ₆ is all a mountain. Non-limiting examples of some glyceryl / acid compounds of the present invention are shown below:

Glyceryl / acid compounds and their derivatives and modifications can be prepared using conventional chemical synthesis techniques (see, for example, Organic Chemistry, 5 ^th Ed.).

2. Glycol / Acid Compound

The glycol / acid compounds of the invention can be derived from glycol molecules. Glycols are a general class of alcohols having two hydroxyl groups. Non-limiting examples of glycols that can be used in the context of the present invention include the following: ethylene glycol (eg, 1,2-ethane diol (monoethylene glycol), 2-hydroxyethoxy) ethan-2-ol (Diethylene glycol); Polyethylene glycols (PEGs); Propylene glycol (eg, 1,2-propane diol, 1,3-propane diol, and the like); And butylene glycol (eg, 1,2-butane diol, 1,3-butane diol, 1,4-butane diol, and the like). Other non-limiting examples of glycols that can be used in the context of the present invention are described in International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed., 2004, which is added by reference. In some aspects, the glycol used may have similar physical and chemical properties as glycerol.

The acid moiety of the glycol / acid compound may be bound via an ester bond of the OH group of the glycol molecule and the COOH group of the acid molecule. In non-limiting aspects, the glycol / acid compound may have the following general chemical structure:

Wherein n can be 2, 3, 4, 5, 6, 7, 8, 9, 10, or more, or any range therein. In some aspects, n is an integer from 2 to 4. Y ₁ , Y ₂ , Y ₃ , and Y ₄ are each independently OY ₅ , H, acid molecules bonded via ester bonds, hydroxy, halogen, oxo (eg ether), alkoxy, silyloxy, acyl , Aryl, acetyl, carbonyl, cyano, heterocyclyl, amido, aminocarbonyl, amino, -NH-alkyl, -N (alkyl) ₂ , -NH- (substituted alkyl), -N- (substituted Alkyl) ₂ , -NH-aryl, -N (aryl) ₂ , azido, trialkylsilyloxy, acyloxy, acylamino, bis-acylamino, ester, NO, NO ₂ , or sulfo (eg, Thioether, thioester, thiocarbonyl, sulfonamido, sulfonyl, etc.). In some aspects, the acid molecule is selected from the group consisting of salicylic acid, cinnamic acid, and benzoic acid, and derivatives and substituted acids thereof. Other non-limiting examples of acids that can be used in the context of the present invention are described in International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed., 2004, which is added by reference. Y ₅ may be any of the groups identified for Y ₁ , Y ₂ , Y ₃ , and Y ₄ . In some aspects Y ₅ is an acid group. In other embodiments, two or more Y ₁ , Y ₂ , Y ₃ , and Y ₄ are hydroxyl groups. Non-limiting examples of some specific glycol / acid compounds of the present invention are shown below:

Glycol / acid compounds and their derivatives and modifications can be prepared using conventional chemical synthesis techniques (see, for example, Organic Chemistry, 5 ^th Ed.).

3. Variants and Derivatives of Glyceryl / Glycol / Acid Compounds

Variants or derivatives of the glyceryl / acid and glycol / acid compounds disclosed throughout this specification are intended to be useful in the methods and compositions of the present invention. Derivatives and modifications can be made and the properties of such derivatives and modified compounds can be analyzed for their desired properties by any method known to those skilled in the art.

In some aspects, “derivative” refers to a chemically modified glyceryl / acid or glycol / acid compound that retains the desired effect of the compound prior to chemical modification. Such derivatives may have the addition, removal, or substitution of one or more chemical moieties in the glyceryl, glycol, and / or acid moieties of the compound. Non-limiting examples of modifications in which these portions of the compound can be prepared include alkyl groups, carboxyl groups, carbonyl groups, hydroxyl groups, nitro groups, amino groups, amide groups, azo groups, sulfate groups, sulfonate groups, sulfono groups, Addition or removal of sulfidyl groups, sulfonyl groups, sulfoxy groups, phosphate groups, phosphono groups, phosphoryl groups, and / or halide groups. Additional modifications may include the addition or removal of one or more atoms of the atomic backbone, eg, substitution of ethyl by propyl or substitution of phenyl by larger or fewer aromatic groups. In cyclic or bicyclic structures, heteroatoms such as N, S, or O may be substituted into the structure instead of carbon atoms.

B. Composition

The compounds of the present invention can be added into all types of compositions (eg, cosmetic and pharmaceutical compositions). Those skilled in the art will appreciate that the composition may comprise any number of combinations of glyceryl / acid compounds, glycol / acid compounds, and / or additional components, or derivatives thereof. Concentrations of glyceryl / acid compounds, glycol / acid compounds, and / or additional ingredients, or derivatives thereof, may vary for a given composition. This change often depends on the desired properties of the final composition. In a non-limiting embodiment, for example, the compositions are in their final form, for example, at least about 0.0001% of one or more glyceryl / acid compounds, glycol / acid compounds, and / or additional ingredients, or derivatives thereof, 0.0002%, 0.0003%, 0.0004%, 0.0005%, 0.0006%, 0.0007%, 0.0008%, 0.0009%, 0.0010%, 0.0011%, 0.0012%, 0.0013%, 0.0014%, 0.0015%, 0.0016%, 0.0017%, 0.0018% , 0.0019%, 0.0020%, 0.0021%, 0.0022%, 0.0023%, 0.0024%, 0.0025%, 0.0026%, 0.0027%, 0.0028%, 0.0029%, 0.0030%, 0.0031%, 0.0032%, 0.0033%, 0.0034%, 0.0035 %, 0.0036%, 0.0037%, 0.0038%, 0.0039%, 0.0040%, 0.0041%, 0.0042%, 0.0043%, 0.0044%, 0.0045%, 0.0046%, 0.0047%, 0.0048%, 0.0049%, 0.0050%, 0.0051%, 0.0052%, 0.0053%, 0.0054%, 0.0055%, 0.0056%, 0.0057%, 0.0058%, 0.0059%, 0.0060%, 0.0061%, 0.0062%, 0.0063%, 0.0064%, 0.0065%, 0.0066%, 0.0067%, 0.0068% , 0.0069%, 0.0070%, 0.0071%, 0.0072%, 0.0073%, 0.0074%, 0.0075%, 0.0076%, 0.0077%, 0.0078%, 0.0079%, 0.0080%, 0.0081%, 0.0082%, 0.0083%, 0.0084 %, 0.0085%, 0.0086%, 0.0087%, 0.0088%, 0.0089%, 0.0090%, 0.0091%, 0.0092%, 0.0093%, 0.0094%, 0.0095%, 0.0096%, 0.0097%, 0.0098%, 0.0099%, 0.0100%, 0.0200%, 0.0250%, 0.0275%, 0.0300%, 0.0325%, 0.0350%, 0.0375%, 0.0400%, 0.0425%, 0.0450%, 0.0475%, 0.0500%, 0.0525%, 0.0550%, 0.0575%, 0.0600%, 0.0625% , 0.0650%, 0.0675%, 0.0700%, 0.0725%, 0.0750%, 0.0775%, 0.0800%, 0.0825%, 0.0850%, 0.0875%, 0.0900%, 0.0925%, 0.0950%, 0.0975%, 0.1000%, 0.1250%, 0.1500 %, 0.1750%, 0.2000%, 0.2250%, 0.2500%, 0.2750%, 0.3000%, 0.3250%, 0.3500%, 0.3750%, 0.4000%, 0.4250%, 0.4500%, 0.4750%, 0.5000%, 0.5250%, 0.0550%, 0.5750%, 0.6000%, 0.6250%, 0.6500%, 0.6750%, 0.7000%, 0.7250%, 0.7500%, 0.7750%, 0.8000%, 0.8250%, 0.8500%, 0.8750%, 0.9000%, 0.9250%, 0.9500%, 0.9750% , 1.0%, 1.1%, 1.2%, 1.3%, 1.4%, 1.5%, 1.6%, 1.7%, 1.8%, 1.9%, 2.0%, 2.1%, 2.2%, 2.3%, 2.4%, 2.5%, 2.6 %, 2.7%, 2.8%, 2.9%, 3.0%, 3.1%, 3.2%, 3.3%, 3.4%, 3.5%, 3.6%, 3.7%, 3.8%, 3.9%, 4.0%, 4.1%, 4.2%, 4.3%, 4.4%, 4.5%, 4.6%, 4.7%, 4.8%, 4.9%, 5.0%, 5.1% , 5.2%, 5.3%, 5.4%, 5.5%, 5.6%, 5.7%, 5.8%, 5.9%, 6.0%, 6.1%, 6.2%, 6.3%, 6.4%, 6.5%, 6.6%, 6.7%, 6.8 %, 6.9%, 7.0%, 7.1%, 7.2%, 7.3%, 7.4%, 7.5%, 7.6%, 7.7%, 7.8%, 7.9%, 8.0%, 8.1%, 8.2%, 8.3%, 8.4%, 8.5%, 8.6%, 8.7%, 8.8%, 8.9%, 9.0%, 9.1%, 9.2%, 9.3%, 9.4%, 9.5%, 9.6%, 9.7%, 9.8%, 9.9%, 10%, 11% , 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28 %, 29%, 30%, 35%, 40%, 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 99% or there It may be included in any range that can be derived. In certain non-limiting aspects, the percentage can be calculated by weight or volume of the total composition. Those skilled in the art will appreciate that concentrations may vary depending on the addition, substitution, and / or reduction of glyceryl / acid compounds, glycol / acid compounds, and additional components, or derivatives thereof.

C. Additional Ingredients

In addition to the glyceryl / acid compounds and / or glycol / acid compounds disclosed herein, the compositions of the present invention may include additional ingredients such as cosmetic ingredients and pharmaceutically active ingredients. Non-limiting examples of these additional ingredients are described in the subsections below.

1. Cosmetic Ingredients

The CTFA International Cosmetic Ingredient Dictionary and Handbook (2004) describes a wide variety of non-limiting cosmetic ingredients that can be used in the context of the present invention. Examples of these component families include: perfume (artificial and natural), dye and color components (eg blue 1, blue 1 lake, red 40, titanium dioxide, D & C blue no. 4, D & C green no. 5, D & C orange no. 4, D & C red no. 17, D & C red no. 33, D & C violet no. 2, D & C yellow no. 10, and D & C yellow no. 11), adsorbents, lubricants, solvents, humectants (e.g. For example, including softeners, wetting agents, film formers, sealants, and agents that affect the natural moisturizing mechanism of the skin), waterproofing agents, UV absorbers (physical and chemical absorbents such as paraaminobenzoic acid ("PABA") and corresponding PABA derivatives, titanium dioxide, zinc oxide, etc.), essential oils, vitamins (eg A, B, C, D, E, and K), trace metals (eg zinc, calcium and selenium), anti- Stimulants (eg steroids and nonsteroidal anti-inflammatory agents), plant extracts (eg aloe vera, camo Sun, cucumber extract, ginkgo biloba, ginseng, and rosemary), antibacterial, antioxidants (eg BHT and tocopherol), chelating agents (eg disodium EDTA and tetrasodium EDTA), preservatives (eg Methylparabens and propylparabens), pH adjusting agents (e.g. sodium hydroxide and citric acid), adsorbents (e.g. aluminum starch octenylsuccinate, kaolin, corn starch, oat starch, cyclo Dextrins, talc, and zeolites), skin lightening and lightening agents (e.g. hydroquinone and nicotinamide amide lactate), humectants (e.g. sorbitol, urea, and mannitol), exfoliants, waterproofing agents (e.g. Magnesium / aluminum hydroxide stearate), skin conditioning agents (e.g., aloe extract, allantoin, bisabolol, ceramide, dimethicone, hyaluronic acid, and dipotassium glycyrrhizate (glycyrrhiz) ate)). Non-limiting examples of some of these components are provided in the subsections below.

a. antiseptic

Non-limiting examples of preservatives that may be used in the context of the present invention include quaternary ammonium preservatives such as polyquaternium-1 and benzalkonium halides (eg, benzalkonium chloride ("BAC") and benz) Alcoholic bromide), parabens (eg, methylparaben and propylparaben), phenoxyethanol, benzyl alcohol, chlorobutanol, phenol, sorbic acid, thimerosal or combinations thereof.

b. Moisturizer

Non-limiting examples of humectants that can be used with the compositions of the present invention can be found in the International Cosmetic Ingredient Dictionary, 10 ^th Ed., 2004. Examples are amino acids, chondroitin sulfate, diglycerin, erythritol, fructose, glucose, 1,2,6-hexanetriol, honey, hyaluronic acid, hydrogenated honey, hydrogenated starch hydrolysates, inositol, lac Titanium, maltitol, maltose, mannitol, natural moisturizing factors, salts of pyrrolidone carboxylic acid, potassium PCA, sodium glucuronate, sodium PCA, sorbitol, sucrose, trehalose, urea, and xylitol.

c. Softener

Non-limiting examples of emollients include, but are not limited to, plant oils, mineral oils, silicone oils, synthetic and natural waxes, mineral oils, lanolin, aluminum magnesium hydroxide stearate (which may also function as a waterproofing agent), and fatty acid esters. Do not. Non-limiting examples of plant oils include safflower oil, corn oil, sunflower seed oil, and olive oil.

d. Antioxidant

Non-limiting examples of antioxidants include acetyl cysteine, ascorbic acid, ascorbic acid polypeptide, ascorbyl dipalmitate, ascorbyl methylsilanol pectate, ascorbyl palmitate, ascorbyl stearate, BHA, BHT , t-butyl hydroquinone, cysteine, cysteine HCl, diamylhydroquinone, di-t-butylhydroquinone, disetyl thiodipropionate, dioleyl tocopheryl methylsilanol, disodium ascorbyl sulfate, distea Reyl thiodipropionate, ditridecyl thiodipropionate, dodecyl gallate, erythorbic acid, esters of ascorbic acid, ethyl ferulate, ferulic acid, gallic acid ester, hydroquinone, isooctyl thioglycolate, kojic acid Rust, magnesium ascorbate, magnesium ascorbyl phosphate, methylsilanol ascorbate, natural vegetable antioxidant Or grape seed extract, nordihydroguaiaretic acid, octyl gallate, phenylthioglycolic acid, potassium ascorbyl tocopheryl phosphate, potassium sulfite, propyl gallate, quinone, rosmarinic acid, sodium ascorbate, sodium Bisulfite, sodium erythorbate, sodium metabisulfite, sodium sulfite, superoxide dismutas, sodium thioglycolate, sorbitol perfural, thiodiglycol, thiodiglycolamide, thiodiglycolic acid, thioglycolic acid , Thiolactic acid, thiosalicylic acid, tocopheris-5, tocopheris-10, tocopheris-12, tocopheris-18, tocopheris-50, tocopherol, tocophersollan, tocopheryl acetate, tocopheryl linoleate, tocopheryl nico Tinate, tocopheryl succinate, and tris (nonylphenyl) phosphite.

e. Thickener

Thickeners, including thickeners or gelling agents, include substances that can increase the viscosity of the composition. Thickeners include those that can increase the viscosity of a composition without substantially altering the efficacy of the components in the composition. Thickeners can also increase the stability of the compositions of the present invention. Non-limiting examples of additional thickeners known to those skilled in the art can be used in the context of the present invention (eg, US Pat. Nos. 5,087,445; 4,509,949; 2,798,053; International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed. , 2004). Examples include carboxylic acid polymers, crosslinked polyacrylate polymers, polyacrylamide polymers, polysaccharides, and gums. Examples of carboxylic acid polymers include crosslinked compounds comprising acrylic acid, substituted acrylic acid, and one or more monomers derived from esters and salts of these acrylic and substituted acrylic acids, wherein the crosslinker comprises two or more carbon-carbon double bonds And derived from polyhydric alcohols. Examples of commercially available carboxylic acid polymers include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol (eg, Carbopol ™ 900 series from BF Goodrich).

f. Silicone-containing compounds

In a non-limiting aspect, the silicon-comprising compound includes any component of the family of polymeric products having a molecular skeleton of alternating silicon and oxygen atoms with side chains that bind to silicon atoms. By changing the -Si-O- chain length, side chains, and crosslinking, silicones can be made into a very wide range of materials. They can change from liquid to gel in a consistent manner.

Silicone-comprising compounds that can be used in the context of the present invention include those described herein or those known to those skilled in the art. Non-limiting examples include silicone oils (eg, volatile and non-volatile oils), gels, and solids. The silicon-comprising compound can be a silicone oil such as polyorganosiloxane. Non-limiting examples of polyorganosiloxanes include dimethicone, cyclomethicone, polysilicon-11, phenyl trimethicone, trimethylsilylamodimethicone, stearoxytrimethylsilane, or mixtures thereof and other organosiloxane materials with desirable consistency. And in any given ratio to achieve application properties that depend on the intended application (eg, to a particular range such as skin, hair, or eyes). "Volatile silicone oil" includes silicone oils having low heat evaporation, that is, normally less than about 50 cal per gram of silicone oil. Non-limiting examples of volatile silicone oils include: cyclomethicones such as Dow Corning 344 Fluid, Dow Corning 345 Fluid, Dow Corning 244 Fluid, and Dow Corning 245 Fluid, Volatile Silicone 7207 (Union Carbide, Dan) Bury, Connecticut); Low viscosity dimethicones, ie dimethicones having a viscosity of about 50 cst or less (eg, dimethicones such as Dow Corning 200-0.5 cst fluid). Dow Corning Fluid is available from Dow Corning, Midland, Michigan. Cyclomethicones and dimethicones are mixtures of fully methylated linear siloxane polymers end-blocked with cyclic dimethyl polysiloxane compounds and trimethylsiloxy units, respectively, in the International Cosmetic Ingredient Dictionary, 10 ^th Ed., 2004. It is described as. Other non-limiting volatile silicone oils that can be used in the context of the present invention include those available from SWS Silicone Div., Adrian, MI of General Electric, Silicon Products Div., Waterford, NY, and Starwoo Chemical.

2. Pharmaceutical Activity

Pharmaceutically active agents are also intended to be useful with the compositions of the present invention. Non-limiting examples of pharmaceutical actives include anti-acne agents, drugs used to treat rosacea, analgesics, anesthetics, anorectals, antihistamines, anti-inflammatory agents including nonsteroidal anti-inflammatory agents, antibiotics, antifungal agents, anti- Antiviral agents, antibacterial agents, anticancer agents, anti-enhancing drugs, ear insecticides, anti-neoplastic agents, limiting agents, anti-itch agents, psoriasis treatment agents, anti-seborrheic agents, biologically active proteins and peptides, burn remedies, cauterizing agents, decolorants, Hair Loss Agents, Diaper Rash Agents, Enzymes, Hair Growth Stimulants, Hair Growth Retardants, Hemostatic Agents, Hemolytic Agents, Thrush Treatments, Herpes Simplex Treatments, Teeth and Periodontal Treatments, Photosensitizers, Skin Protectors / Steroids including sunscreens, hormones and corticosteroids, sunburn agents, sunscreen agents, transdermal active agents, nasal active agents, vaginal active agents, warts Ear treatments, wound healing agents, wound healing agents, and the like.

D. Vehicle

The composition of the present invention can be added into any form of vehicle. Non-limiting examples of suitable vehicles include emulsions (e.g., by other methods or any combination previously known to those skilled in the art (see, eg, Remington's, 1990 and International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed., 2004). For example, lipophilic emulsification, water-in-oil-in-water, hydrophilic emulsification, oil-in-water-in-oil, oil-in-water-in-silicone, water-in-silicone, silicone-in- Water emulsions), creams, lotions, solutions (both water soluble and hydro-alcoholic), anhydrous bases (such as lipsticks and powders), gels, and ointments. Variations and other suitable vehicles will be apparent to those skilled in the art and are suitable for use in the present invention. In some aspects, it is important that the concentrations and combinations of compounds, components, and agents are selected in such a way that the combination is chemically compatible and no complexes precipitate from the final product.

E. Cosmetic Products and Manufacturing Items

The compositions of the present invention are also suitable for sunscreen products, indoor skin tanning products, hair products, nail products, moisturizing creams, creams and lotions beneficial to the skin, emollients, day lotions, gels, ointments, foundations, night creams, lipsticks, cleansers, toners , Masks, or other known cosmetic products or applications can be used in a number of cosmetic products, including but not limited to. In addition, cosmetic products may be formulated as leave-on and rinse-off products. In some aspects, the composition of the present invention is a stand-alone product.

F. Kit

Kits are also intended to be used in some aspects of the invention. For example, the emulsion composition of the present invention can be included in a kit. The kit may comprise a container. The container may be a bottle, a metal tube, a laminate tube, a plastic tube, a dispenser, a pressure container, a barrier container, a package, a compartment, a lipstick container, a compact container, a cosmetic pan that can contain a cosmetic composition, or another type of container such as Plastic containers dispensed or blow-molded into dispersions or compositions or desired bottles, dispensers, or packages to be retained. Indications may be, for example, words, phrases, abbreviations, pictures, or symbols.

The container may dispense a predetermined amount of the emulsion composition. In other embodiments, the container may be squeezed to dispense the desired amount of emulsion composition (eg, metal, laminate, or plastic tube). The emulsion composition may be dispensed as a spray, aerosol, liquid, fluid, or semisolid. The container may have a spray, pump, or squeeze mechanism. The kit may also include instructions for using the kit components as well as the use of any other emulsion composition contained in the container. The instructions may include a description of how to apply, use, and maintain the emulsion composition.

The following examples are included to illustrate some non-limiting aspects of the present invention. It should be recognized by those skilled in the art that the techniques have been disclosed in the Examples and which are followed by the typical techniques found by the inventors to function well in the practice of the invention. However, one of ordinary skill in the art should recognize that changes can be made in the specific embodiments disclosed and still obtain a like or similar result without departing from the spirit and scope of the invention.

Example 1

Process for preparing glyceryl / acid or glycolic acid compound

Esterification processes can be used to prepare glyceryl / acid and glycol / acid compounds. Glyceryl or glycol molecules and acid molecules were added to a multi-necked round bottom flask equipped with heating mantle, condenser, Dean-Stark trap and thermometer. Solvents were selected that were sufficiently capable of high reflux temperatures to control the reaction. The reaction is carried out until a calculated amount of water is collected in the trap indicating a signal that the restriction reagent is exhausted. By-products can be compounds other than water in some processes. For example, if methyl salicylate is used where salicylic acid is present, methanol will be a by-product in addition to water, and methanol may escape through the condenser or remain in the reaction flask. Methanol can be removed when the ester is extracted.

Example 2

UV Absorption Data for Glyceryl Mono-S Alkylate

UV absorption data for glyceryl mono-salicylate is summarized in Table 1 below:

Table 1 (UV absorption data ^* )

^* Data obtained by UV / Vis spectrometer using standard USP 197U test method.

Example 3

Composition

Non-limiting examples of the compositions of the present invention are listed in Tables 1-3.

TABLE 2 ^*  (Peeling composition)

^* The composition is prepared as follows: mixing and chilling the component was added to the beaker in the order listed before adding the next ingredient. The pH of the composition was adjusted to approximately 4.3 using 1N HCl solution. ^** Glyceryl mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

TABLE 3 ^*  (Moisturizer ^** )

^The composition was prepared as follows: Phases A and B were heated to approximately 70 ° C.-75 ° C. while mixing in separate beakers. Phase B was added to phase A when both phases were approximately 70 ° -75 ° C. The phase A + B mixture was cooled to <40 ° C. while mixing. Phase C was added sequentially to the phase A + B mixture and the mixture was cooled to room temperature (approximately 20 ° C.-25 ° C.) while mixing.

^** Formulation shows statistically significant moisturization for 6 hours after application to skin compared to baseline control (p <0.05) (data not shown).

^*** Glyceryl mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

Table 4 (General Formulations) ^*

^The composition was prepared as follows: Xanthan gum was sprayed on water and mixed for 10 minutes. Next, all components of phase A were added and heated to 70-75 ° C. All items of phase B were added to a separate beaker and heated to 70-75 ° C. Phases A and B were mixed at 70-75 ° C. It was then mixed and the composition was allowed to cool to 30 ° C. Next, add phase C components while mixing.

^** Glyceryl mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

Table 5 (General Formulations) ^*

^* With respect to the components in the phase A was added to the beaker and the mixture was heated to 70-75 ℃. The components of phase B were then added to phase A and cooled to 30 ° C. while mixing. Next, add phase C components while mixing.

^** Glyceryl mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

Table 6 (General Formulations) ^*

^The composition was prepared as follows: Xanthan gum was sprayed on water and mixed for 10 minutes. Next, all components of phase A were added and heated to 70-75 ° C. All items of phase B were added to a separate beaker and heated to 70-75 ° C. Phases A and B were mixed at 70-75 ° C. It was then mixed and the composition was allowed to cool to 30 ° C. Next, add phase C components while mixing.

^** Glyceryl Mono-salicylate and / or Glycol Mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

Table 7 (General Formulations) ^*

^* The A component was added to the beaker and the mixture was heated to 70-75 ℃. The components of phase B were then added to phase A and cooled to 30 ° C. while mixing. Next, add phase C components while mixing.

^** Glyceryl Mono-salicylate and / or Glycol Mono-salicylate can be substituted with other glyceryl / acid and glycol / acid compounds.

Example 4

Determination of Efficacy of Glyceryl / Acid or Glycol / Acid Compounds and Compositions

The efficacy of glyceryl / acid or glycol / acid compounds and compositions comprising them can be measured by methods known to those skilled in the art. The following are non-limiting methods that can be used in the background of the present invention. It should be appreciated that other methods may be used, including, for example, objective and subjective methods.

Skin moisture / hydration can be measured using an impedance measurement method in conjunction with a Nova Dermal Phase Meter. Impedance meters measure the change in skin moisture content. The outer layer of skin has unique electrical properties. As your skin dries, it conducts very little electricity. The more hydrated, the higher the conductivity. In conclusion, changes in skin impedance can be used to assess changes in skin hydration (related to conductivity). The unit can be calibrated according to the instrument instructions for each test day. In addition, the notation of temperature and relative humidity can also be made. Subjects can be evaluated as follows: Equilibrium can be equilibrated at room temperature with defined humidity (eg 30-50%) and temperature (eg 68-72 ° C.) prior to measurement. Three separate impedance readings are performed on each side of the face, recorded and averaged. The T5 setting can be used on an impedance meter that averages the impedance value applied to the face every 5 seconds. Changes can be recorded with statistical variability and importance.

Skin clarity and reduction of freckles and blotch can be assessed using Minolta Chromometer. Changes in skin color can be evaluated to determine the stimulus potential due to product treatment using the a * value of the Minolta chromometer. The a * value measures the change in skin color in the red region. This is used to determine whether the composition induced stimulation. Measurements can be made on each side of the face and averaged as left and right facial values. Skin transparency can also be measured using a Minolta meter. The measurement is a combination of the a *, b, and L values of the Minolta meter and is related to skin brightness and well related to skin smoothness and hydration. Skin reading is performed as described above. In one non-limiting aspect, skin clarity can be described as L / C, where C is chromaticity and is defined as (a ² + b ² ) ^1/2 .

Skin dryness, surface thin lines, skin smoothness, and skin tone can be evaluated as clinical grading techniques. For example, the clinical grade of skin dryness can be measured by five standard Krigman scales: (0) skin soft and moist; (1) the skin appears normal without visible dryness; (2) the skin feels slightly dry with no visible flakes; (3) the skin feels dry and rough and has a slightly white appearance with some scalyness; And (4) the skin feels very dry and rough and has a slightly white appearance with scalyness. Evaluation is done by two clinicians independently and averaged.

Clinical grades of skin tone can be performed through 10 analog numeric scales: (10) even, pinkish brown flat skin. Inspected by hand, dark, erythremic, or scaly patches are captured by the magnifying lens. Microstructure of the skin feels very flat; (7) Flat skin tone observed without magnification. No area with scales, but slight discoloration due to pigmentation or erythema. No discoloration of diameters greater than 1 cm; (4) Skin discoloration and uneven tissues are easily visible. Slight scaliness. The skin feels rough in some areas; And (1) uneven skin discoloration and tissue. Scaly and pigmented, low dyeing, erythropathic or dark spots in many parts. Uneven color in large areas with a diameter larger than 1 cm. Evaluation is done by two clinicians independently and averaged.

The clinical grade of skin smoothness can be analyzed on 10 analog numeric scales: (10) smoothness, skin is moist and shiny, no resistance to finger scrubbing; (7) slightly smooth, slightly resistant; (4) rough, visually altered, rubbing when rubbed; And (1) rough, flaky, uneven surfaces. Evaluation is done by two clinicians independently and averaged.

Skin smoothness and wrinkle reduction can also be assessed visually by using the methods disclosed in Packman and Gams (1978). For example, as each individual visits, the depth, shallowness and total number of facial lines (SFLs) on the surface of each individual are carefully scored and recorded. The score is obtained by multiplying the number of factors by the depth / width / length factor. Scores are obtained for the eye area and mouth area (left and right sides) and added together as wrinkle scores.

Skin firmness can be measured using a Hargens ballistometer, a device that measures the elasticity and firmness of the skin by dropping a small body onto the skin and recording its first two rebound peaks. Ballastometers are small, lightweight probes with relatively blunt tips (4 square mm-contact range) used. The probe penetrates slightly into the skin, resulting in a measurement that depends on the properties of the outer layers of skin including the stratum corneum and outer epidermis and some dermis layers.

Skin softness / flexibility can be assessed using a Gas Bearing Electrodynamometer, a device that measures the stress / strain properties of the skin. The viscoelastic properties of the skin are related to the moisturizing of the skin. By attaching the probe to the skin surface with a double-stick tape the measurement can be obtained at a predetermined location on the check range. Approximately 3.5 gm of force can be applied parallel to the skin surface and skin displacement is accurately measured. Skin flexibility is then calculated and expressed as the Dynamic Spring Rate in gm / mm.

The appearance of lines and wrinkles on the skin can be assessed using replicas that are impressions of the surface of the skin. Materials such as silicone rubber can be used. Replicas can be analyzed by image analysis. Changes in the visibility of lines and wrinkles can be objectively quantified by obtaining a silicon replica of the subject's face and analyzing the replica image using a computer image analysis system. Replicas may be obtained from the eye and neck areas, and may be photographed with a digital camera using low angle incident illumination. The digital image can be analyzed with an image processing program and the duplicates are covered by the wrinkles or fine lines being measured.

The surface contour of the skin can be measured using the profilometer / Stylus method. This involves shining light or sweeping the stylus across the replica surface. The vertical displacement of the stylus can be fed into the computer through a distance transducer and an analysis of the cross section of the skin profile after scanning a fixed length replica can be generated as a two-dimensional curve. This scan can be repeated any number of times along a fixed axis to produce a simulated 3-D picture of the skin. Ten random parts of the replica using the stylus technique can be obtained and combined to produce an average value. Interesting values are the arithmetic mean of all roughness (height) values calculated by integrating the profile heights associated with the average profile height, Rt, the maximum vertical distance between the highest and lowest valleys, and the average peak width minus the average peak. Contains Rz which is the height. The value is given as the value tested in mm. The device must each be standardized prior to use by scanning metal standards of known values. The Ra value can be calculated by the formula: Ra = normalized roughness; l m = horizontal sheer (scan) length; And y = complete value of the position of the profile with respect to the average profile height (x-axis).

In another non-limiting aspect, the efficacy of the compositions of the present invention can be assessed by using skin analogs such as MELANODERM ™. Melanosite, one of the cells in the skin analog, is clearly colored when exposed to L-dihydroxyphenyl alanine (L-dopa), a precursor of melanin. MELANODERM ™, a skin analog, can be treated with various bases comprising the composition and the whitening agent of the invention or treated with base alone as a control. Alternatively, an untreated sample of skin analog can be used as a control.

UV absorption of glyceryl / acid or glycol / acid compounds and compositions comprising them can be measured by UV absorption assays generally known to those skilled in the art.

All compounds, compositions, and / or methods disclosed and claimed may be made and performed without undue experimentation in light of the present disclosure. While the compounds, compositions, and methods of the present invention have been described in terms of some embodiments, changes may be made in the steps of a method or in a series of steps without departing from the spirit, scope, and scope of the invention. And / or be applicable to the methods will be apparent to those skilled in the art. More specifically, it will be apparent that some agents, both chemically and physically related, may be substituted for the agents described herein while achieving the same or similar results. All such similar substituents and modifications apparent to those skilled in the art are considered to be within the concept, spirit and scope of the invention.

references

To the extent that such procedures are provided by way of typical procedures or other detailed supplements, the following references are hereby expressly incorporated by reference.

U.S. Patent No. 2,798,053

U.S. Patent 4,509,949

U.S. Patent 5,087,445

CTFA International Cosmetic Ingredient Dictionary and Handbook, 10 ^th Ed., (2004).

Organic Chemistry, 5th Ed.

Packman and Gams, J. Soc. Cos. Chem., 29: 70-90, 1978.

Remington's Pharmaceutical Sciences, 18th Ed. Mack Printing Company, 1289-1329, 1990.

Claims (36)

A topical skin care composition comprising a glyceryl salicylate compound or a glycol salicylate compound. The topical skin care composition of claim 1, wherein the composition comprises a glyceryl salicylate compound having the structure

Wherein R, R ₄ , and R ₆ are each independently H, salicylic acid molecules, or alkyl groups, provided that at least one of R, R ₄ , and R ₆ is a salicylic acid molecule; R ₁ , R ₂ , R ₃ , R ₅ , and R ₇ are each independently H or an alkyl group. The topical skin care composition of claim 2, wherein R is salicylic acid and R ₄ and R ₆ are each H. ₄ . The topical skin care composition of claim 2, wherein the compound has the structure

The topical skin care composition of claim 4, wherein the composition further comprises a glyceryl di-salicylate compound or a glyceryl tri-salicylate compound. The topical skin care composition of claim 5, wherein the composition further comprises a glyceryl di-salicylate compound and a glyceryl tri-salicylate compound. The topical skin care composition of claim 2, wherein R ₆ is salicylic acid and R and R ₄ are each H. ₄ . 8. A topical skin care composition according to claim 7, wherein said compound has the structure:

The topical skin care composition of claim 2, wherein R and R ₆ are each salicylic acid and R ₄ is H. ₄ . 10. The topical skin care composition of claim 9, wherein said composition further comprises a glyceryl di-salicylate compound or a glyceryl tri-salicylate compound. The topical skin care composition of claim 10, wherein the composition further comprises a glyceryl di-salicylate compound and a glyceryl tri-salicylate compound. The topical skin care composition of claim 9, wherein the compound has the structure:

The topical skin care composition of claim 12, wherein the composition further comprises a glyceryl mono-salicylate compound or a glyceryl tri-salicylate compound. The topical skin care composition of claim 13, wherein the composition further comprises a glyceryl mono-salicylate compound and a glyceryl tri-salicylate compound. The topical skin care composition of claim 2, wherein R and R ₄ are each salicylic acid and R ₆ is H. ₄ . The topical skin care composition of claim 15, wherein the compound has the structure:

The topical skin care composition of claim 16, wherein the composition further comprises a glyceryl mono-salicylate compound or a glyceryl tri-salicylate compound. 18. The topical skin care composition of claim 17, wherein said composition further comprises a glyceryl mono-salicylate compound and a glyceryl tri-salicylate compound. The topical skin care composition of claim 2, wherein R, R ₄ and R ₆ are each salicylic acid. The topical skin care composition of claim 19, wherein the compound has the structure:

The topical skin care composition of claim 20, wherein the composition further comprises a glyceryl mono-salicylate compound or a glyceryl di-salicylate compound. The topical skin care composition of claim 21, wherein the composition further comprises a glyceryl mono-salicylate compound and a glyceryl di-salicylate compound. The topical skin care composition of claim 1, wherein the composition comprises a glycol salicylate compound selected from the group consisting of ethylene glycol salicylate and propylene glycol salicylate. The topical skin care composition of claim 23, wherein said composition comprises an ethylene glycol salicylate compound selected from the group consisting of:

The topical skin care composition of claim 23, wherein said composition comprises a propylene glycol salicylate compound selected from the group consisting of:

The topical skin care composition of claim 1, wherein said composition comprises a glyceryl salicylate compound and a glycol salicylate compound. The topical skin care composition of claim 1, wherein said composition is an emulsion, cream, lotion, or ointment. The topical skin care composition of claim 1, wherein said composition is an anhydrous composition. The topical skin care composition of claim 1, wherein the composition comprises about 0.001% to about 20% by weight of the compound. The topical skin care composition of claim 1, wherein said composition absorbs UV light. A method of treating a skin condition comprising topically applying the composition of claim 1 to the skin, wherein topical application of the composition to the skin treats the skin condition. 32. The method of claim 31 wherein said skin condition is fine lines or wrinkles.  32. The method of claim 31, wherein said skin condition is dry skin. A method of reducing the amount of water evaporated from the skin comprising topically applying the composition of claim 1 to the skin, wherein topical application of the composition forms a film on the skin that reduces the amount of water evaporated from the skin. Way. A method of protecting the skin from UV light comprising topically applying the composition of claim 1 to the skin, wherein the composition absorbs UV light. A method of protecting a composition from chemical or physical deterioration caused by UV light comprising adding a glyceryl salicylate molecule or an effective amount of a glycol salicylate molecule to the composition, wherein the glyceryl salicylate Or the glycol salicylate molecule absorbs UV light.